ChemInform Abstract: Reaction of β-Ethylthiopropionyl Tetrafluoroborates with Alkynes. Stereospecific One-Pot Synthesis of 1-Ethylthiopenta-1,4-dien-3-ones.
Abstract
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ChemInform Abstract
β-Ethylthiopropionyl tetrafluoroborate, in situ generated from the corresponding acyl fluoride (II) and gaseous BF3, reacts with alkynes (I) to form the hitherto unknown products (III) of a regio- and stereospecific syn-addition of acryloyl and ethylthio groups to the triple bond. The reaction proceeds through formation of six-membered cyclic sulfonium salts. Interestingly, treatment of (IIIc) with perchloric acid results in recyclization to the cyclic sulfonium structure (IV).
